1,2-Dichloroethane → 2-ethyl-6-methyl-isonicotinic acid N'-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carbonyl)-hydrazide

HRID 1924830Notes

Reaction equation

HRID 1924830 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:6]([OH:8])=O)[CH3:2].[CH3:13][C:14]1([CH3:28])[CH:16]2[CH2:17][C:18]3[C:22]([CH:15]12)=[C:21]([CH3:23])[S:20][C:19]=3[C:24]([NH:26][NH2:27])=[O:25].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[CH3:13][C:14]1([CH3:28])[CH:16]2[CH2:17][C:18]3[C:22]([CH:15]12)=[C:21]([CH3:23])[S:20][C:19]=3[C:24]([NH:26][NH:27][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([CH3:12])[N:11]=[C:3]([CH2:1][CH3:2])[CH:4]=1)=[O:25]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 584180972-Ethyl-6-methylisonicotinic acidHCID 675205611,1,2-Trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid hydrazide

Product 1

HCID 675205712-ethyl-6-methyl-isonicotinic acid N'-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carbonyl)-hydrazideYield 172.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-ethyl-6-methyl-isonicotinic acid (87.9 mg, 0.53 mmol), 1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid hydrazide (141.8 mg, 0.6 mmol), HOBt (100 mg, 0.74 mmol) and TEA (0.42 mL) in DCM (5 mL) is added at 0° C. EDC (200 mg, 0.78 mmol). The mixture is stirred for 15 h during which time it warmed from 0° C. to rt. The mixture is quenched with EA (50 mL) and washed with 1M aq. NaOH (2×10 mL). The organic phase is dried (Na2SO4), filtered and evaporated to give crude 2-ethyl-6-methyl-isonicotinic acid N′-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carbonyl)-hydrazide (350 mg); LC-MS: tR=0.80 min, [M+1]=384.34.

Workup

  1. additionis added at 0° C
  2. temperaturewarmed from 0° C. to rt
  3. customThe mixture is quenched with EA (50 mL)
  4. washwashed with 1M aq. NaOH (2×10 mL)
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d297a34fc9a04416a92fad6613faac04
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

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